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AR063211A1 - DERIVATIVES OF 3- (PIRIDIN-3-IL) ACRILAMIDE AND 3- (PIRIDIN-3-IL) PROPIONAMIDE, A METHOD FOR THEIR PREPARATION, A PHARMACEUTICAL COMPOSITION THAT UNDERSTANDS AND THEIR USE IN THE MANUFACTURE OF MEDICINES FOR THE TREATMENT OF ASSOCIATED DISEASES WITH THE VANILOID RECEIVER. - Google Patents

DERIVATIVES OF 3- (PIRIDIN-3-IL) ACRILAMIDE AND 3- (PIRIDIN-3-IL) PROPIONAMIDE, A METHOD FOR THEIR PREPARATION, A PHARMACEUTICAL COMPOSITION THAT UNDERSTANDS AND THEIR USE IN THE MANUFACTURE OF MEDICINES FOR THE TREATMENT OF ASSOCIATED DISEASES WITH THE VANILOID RECEIVER.

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Publication number
AR063211A1
AR063211A1 ARP070103317A ARP070103317A AR063211A1 AR 063211 A1 AR063211 A1 AR 063211A1 AR P070103317 A ARP070103317 A AR P070103317A AR P070103317 A ARP070103317 A AR P070103317A AR 063211 A1 AR063211 A1 AR 063211A1
Authority
AR
Argentina
Prior art keywords
alkyl
alkoxy
unsubstituted
substituted
halogen
Prior art date
Application number
ARP070103317A
Other languages
Spanish (es)
Original Assignee
Amorepacific Corp
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from EP06015724A external-priority patent/EP1882687A1/en
Application filed by Amorepacific Corp filed Critical Amorepacific Corp
Publication of AR063211A1 publication Critical patent/AR063211A1/en

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    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D419/08—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen, oxygen, and sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing alicyclic rings
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    • C07C311/01—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms
    • C07C311/02—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C311/08—Sulfonamides having sulfur atoms of sulfonamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
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    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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    • C07D295/14—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
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  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Pyridine Compounds (AREA)
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  • Hydrogenated Pyridines (AREA)

Abstract

Sales farmacéuticamente aceptables, como antagonistas del receptor vaniloide (receptor vaniloide 1; VR1; TRPV1); una composicion farmacéutica que las contiene y su uso en la fabricacion de medicamentos para prevenir o tratar una enfermedad como el dolor, migrana, artralgia, neuralgia, neuropatías, lesion nerviosa, trastorno cutáneo, hipersensibilidad de la vejiga urinaria, síndrome de intestino irritable, incontinencia fecal, trastorno respiratorio, irritacion de la piel, ojos o membrana mucosa, ulcera del estomago y duodeno, enfermedades inflamatorias, enfermedad auditiva, enfermedad cardíaca y otras, Se provee además un método para su preparacion. Reivindicacion 1: Un compuesto de la formula (1), su isomero, o una de sus sales farmacéuticamente aceptables: en donde: X es CR11=CR12, o C:::C; en donde, R11 y R12, si están presentes, son independientemente hidrogeno, halogeno o alquilo C1-5; Z es N; Y es CR6; R1 es hidrogeno, halogeno o alquilo C1-5; R2, R3, R4, y R5 son independientemente hidrogeno, halogeno, nitro, ciano, alquilo C1-5, alcoxi C1-5, haloalquilo C1-5, alquenilo C2-5, alquinilo C2-5, carboxi, alcoxicarbonilo C1-5 o alquiltio C1-5; R6 es hidroxi, halogeno, nitro, carboxi, alquil C1-10, alcoxilo C1-10, alquenilo C2-10, alquinilo C2-10, alquil C1-10tio, alquil C1-10sulfonilo, alquil C1-10carbonilo, alcoxilo C1-10carbonilo, alquenilo C2-10oxi, alcoxi C1-5-alcoxi C1-5, alcoxi C1-5-alcoxi C1-5-alquilo C1-5, piperidilo, piperacinilo, alcoxi C1-5-alquil C1-5amino, alquil C1-10amino, di(alquil C1-10)amino, cicloalquil C3-8 , cicloalquil C3-8 amino, cicloalcoxi C3-8, oxacicloalquiloxi C3-8, N-alcoxi C1-5-alquilC1-5-N-alquilC1-5amino, N-cicloalquil C3-8-N-alquil C1-5amino, N-aril-N-alquil C1-5amino, preferiblemente N-fenil-N-alquil C1-5amino, arilo, preferiblemente fenilo, arilamino, preferiblemente fenilamino, aritio, preferiblemente fenitio, heteroarilo, preferiblemente piridinilo o tienilo, heteroarilamino, ariloxi, preferiblemente fenoxi, heteroariloxi, preferiblemente piridiniloxi, pirrolidinilo o morfoIinilo, R8 y R9 son independientemente hidrogeno, hidroxi, halogeno, nitro, carboxi, alquil C1-10, alcoxilo C1-10, alquenilo C2-10, alquinilo C2-10, alquil C1-10tio, alquil C1- 10sulfonilo, alquil C1-10carbonilo, alcoxilo C1-10carbonilo, alquenilo C2-10oxi, alcoxi C1-5-alcoxi C1-5, alcoxi C1-5-alcoxi C1-5-alquilo C1-5, piperidilo, piperacinilo, alcoxi C1-5-alquil C1-5amino, alquil C1-10amino, di(alquil C1-10)amino, cicloalquil C3-8 , cicloalquil C3-8 amino, cicloalcoxi C3-8, oxacicloalquiloxi C3-8, N-alcoxi C1-5-alquilC1-5-N-alquilC1-5amino, N-cicloalquil C3-8-N-alquil C1-5amino, N-aril-N-alquil C1-5amino, preferiblemente N-fenil-N-alquil C1-5amino, arilo, preferiblemente fenilo, arilamino, preferiblemente fenilamino, aritio, preferiblemente fenitio, heteroarilo, preferiblemente piridinilo o tienilo, heteroarilamino, ariloxi, preferiblemente fenoxi, heteroariloxi, preferiblemente piridiniloxi, pirrolidinilo o morfoIinilo, en donde: cada alquilo, alquenilo y alquinilo, también como parte de un grupo tal como en alcoxi, alquilsulfonilo, alquilcarbonilo, alquilamino o alqueniloxi, puede estar independientemente sustituido o no sustituido con uno o más sustituyentes seleccionados de entre halogeno, hidroxilo, alcoxi C1-5 sustituido o no sustituido con una funcionalidad halo, cicloalquilo C3-8 que puede estar sustituido o no sustituido con uno o dos radicales halogeno y/o grupos metilo, alquilamino C1-5 sustituido o no sustituido con una funcionalidad halo, fenilo que puede estar sustituido o no sustituido con uno o más sustituyentes seleccionados de halogeno, alquil C1-3 no sustituido, o haloalquilo C1-3, o di(C1-5)alquilamino sustituido o no sustituido con funcionalidad halo, cada arilo o heteroarilo, también parte de un grupo tal como en arilamino, ariloxi, heteroarilamino o heteroariloxi, puede estar independientemente sustituido o no sustituido con uno o más sustituyentes seleccionados de halogeno, alquilo C1-5 no sustituido, alcoxi C1-5 no sustituido o haloalquilo C1-5, cada cicloalquilo, también como parte de un grupo tal como en el cicloalcoxi o cicloalquilamino, puede estar sustituido o no sustituido con uno o más grupos alquilo C1-3 sustituidos o no sustituidos con funcionalidad halo, hidroximetilo, hidroxi, metoxi o amino, y cada piperacinilo, piperidilo, morfolinilo y pirrolidinilo puede estar sustituido o no sustituido con uno o más grupos alquilo C1-3 sustituidos o no sustituidos con funcionalidad halo, hidroxialquilo C1-3, alcoxi C1-3, alcoxi C1-3carbonilo, o hidroxilo; R7 es haloalquilo C1-5; y R10 es alquilo C1-5, haloalquilo C1-5, o alquenilo C2-5. Reivindicacion 47: Un proceso para la elaboracion de un compuesto representado por la formula (3) que comprende la reaccion de un compuesto representado por la formula (4); con un compuesto representado por la formula (5); en donde: R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 y R12 son como los descritos en una cualquiera de las reivindicaciones precedentes. Reivindicacion 49: Un compuesto de la formula (6) en donde W es hidrogeno o fluoro; R1 es hidrogeno o alquilo C1-3, preferiblemente metilo; y R10 es alquilo C1-3, alquenilo C2-3 o haloalquilo C1-3, preferiblemente metilo; con tal que si R1 es hidrogeno y R10 es metilo, entonces W es fluoro.Pharmaceutically acceptable salts, as vanilloid receptor antagonists (vaniloid receptor 1; VR1; TRPV1); a pharmaceutical composition that contains them and their use in the manufacture of medications to prevent or treat a disease such as pain, migraine, arthralgia, neuralgia, neuropathies, nerve injury, skin disorder, urinary bladder hypersensitivity, irritable bowel syndrome, incontinence fecal, respiratory disorder, irritation of the skin, eyes or mucous membrane, ulcer of the stomach and duodenum, inflammatory diseases, hearing disease, heart disease and others, A method for its preparation is also provided. Claim 1: A compound of the formula (1), its isomer, or a pharmaceutically acceptable salt thereof: wherein: X is CR11 = CR12, or C ::: C; wherein, R11 and R12, if present, are independently hydrogen, halogen or C1-5 alkyl; Z is N; And it is CR6; R1 is hydrogen, halogen or C1-5 alkyl; R2, R3, R4, and R5 are independently hydrogen, halogen, nitro, cyano, C1-5 alkyl, C1-5 alkoxy, C1-5 haloalkyl, C2-5 alkenyl, C2-5 alkynyl, carboxy, C1-5 alkoxycarbonyl or C1-5 alkylthio; R6 is hydroxy, halogen, nitro, carboxy, C1-10 alkyl, C1-10 alkoxy, C2-10 alkenyl, C2-10 alkynyl, C1-10 alkylthio, C1-10 alkyl sulfonyl, C1-10 alkylcarbonyl, C1-10 alkoxycarbonyl, C2-10oxy alkenyl, C1-5 alkoxy-C1-5 alkoxy, C1-5 alkoxy-C1-5 alkoxy-C1-5 alkyl, piperidyl, piperazinyl, C1-5 alkoxy-C1-5amino alkyl, C1-10amino alkyl, di (C1-10 alkyl) amino, C3-8 cycloalkyl, C3-8 cycloalkyl amino, C3-8 cycloalkoxy, C3-8 oxocycloalkyloxy, N-C1-5 alkoxy-C1-5-N-C1-5-amino alkyl, N-C3-alkylalkyl -8-N-C1-5-alkyl, N-aryl-N-C1-5-alkyl, preferably N-phenyl-N-C1-5-alkyl, aryl, preferably phenyl, arylamino, preferably phenylamino, arithium, preferably phenyl, heteroaryl, preferably pyridinyl or thienyl, heteroarylamino, aryloxy, preferably phenoxy, heteroaryloxy, preferably pyridinyloxy, pyrrolidinyl or morphoIinyl, R8 and R9 are independently hydrogen, hydroxy, halogen, nitro, carboxy, C1-10 alkyl, C1-10 alkoxy, al C2-10 quenyl, C2-10 alkynyl, C1-10 alkylthio, C1-10 alkyl sulfonyl, C1-10 alkylcarbonyl, C1-10 alkoxycarbonyl, C2-10oxy alkenyl, C1-5 alkoxy C1-5 alkoxy, C1-5 alkoxy C1-5 alkoxy-C1-5 alkyl, piperidyl, piperazinyl, C1-5 alkoxy-C1-5amino alkyl, C1-10 alkyl, di (C1-10 alkyl) amino, C3-8 cycloalkyl, C3-8 aminocycloalkyl, cycloalkoxy C3-8, C3-8 oxocycloalkyloxy, N-C1-5-alkoxyC1-5-N-C1-5alkyl, N-cycloalkyl C3-8-N-alkyl C1-5amino, N-aryl-N-C1-5amino , preferably N-phenyl-N-C 1-5 alkyl, aryl, preferably phenyl, arylamino, preferably phenylamino, arithium, preferably phenylene, heteroaryl, preferably pyridinyl or thienyl, heteroarylamino, aryloxy, preferably phenoxy, heteroaryloxy, preferably pyridinyloxy, pyrrolidinyl or morpho , wherein: each alkyl, alkenyl and alkynyl, also as part of a group such as alkoxy, alkylsulfonyl, alkylcarbonyl, alkylamino or alkenyloxy, may be independent. wholly substituted or unsubstituted with one or more substituents selected from halogen, hydroxyl, C1-5 alkoxy substituted or unsubstituted with a halo functionality, C3-8 cycloalkyl which may be substituted or unsubstituted with one or two halogen radicals and / or methyl, C1-5 alkylamino groups substituted or unsubstituted with a halo functionality, phenyl which may be substituted or unsubstituted with one or more substituents selected from halogen, unsubstituted C1-3 alkyl, or C1-3 haloalkyl, or di (C1 -5) alkylamino substituted or unsubstituted with halo functionality, each aryl or heteroaryl, also part of a group such as arylamino, aryloxy, heteroarylamino or heteroaryloxy, may be independently substituted or unsubstituted with one or more substituents selected from halogen, alkyl C1-5 unsubstituted, C1-5 alkoxy unsubstituted or C1-5 haloalkyl, each cycloalkyl, also as part of a group such as in the cycloalkoxy or cycloalkylamino, may be tar substituted or unsubstituted with one or more substituted or unsubstituted C1-3 alkyl groups with halo, hydroxymethyl, hydroxy, methoxy or amino functionality, and each piperazinyl, piperidyl, morpholinyl and pyrrolidinyl may be substituted or unsubstituted with one or more groups C1-3alkyl substituted or unsubstituted with halo, C1-3 hydroxyalkyl, C1-3 alkoxy, C1-3alkoxycarbonyl, or hydroxyl functionality; R7 is C1-5 haloalkyl; and R10 is C1-5 alkyl, C1-5 haloalkyl, or C2-5 alkenyl. Claim 47: A process for the preparation of a compound represented by the formula (3) comprising the reaction of a compound represented by the formula (4); with a compound represented by the formula (5); wherein: R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11 and R12 are as described in any one of the preceding claims. Claim 49: A compound of the formula (6) wherein W is hydrogen or fluoro; R1 is hydrogen or C1-3 alkyl, preferably methyl; and R10 is C1-3 alkyl, C2-3 alkenyl or C1-3 haloalkyl, preferably methyl; provided that if R1 is hydrogen and R10 is methyl, then W is fluoro.

ARP070103317A 2006-07-27 2007-07-26 DERIVATIVES OF 3- (PIRIDIN-3-IL) ACRILAMIDE AND 3- (PIRIDIN-3-IL) PROPIONAMIDE, A METHOD FOR THEIR PREPARATION, A PHARMACEUTICAL COMPOSITION THAT UNDERSTANDS AND THEIR USE IN THE MANUFACTURE OF MEDICINES FOR THE TREATMENT OF ASSOCIATED DISEASES WITH THE VANILOID RECEIVER. AR063211A1 (en)

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